Sodium Hydroxide → HCID 19690917, compound

HRID 441575Notes

Reaction equation

HRID 441575 reaction equation
C([NH:4][CH:5]([CH3:18])[CH2:6][C:7]1[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:9][CH:8]=1)(=O)C.[OH-].[Na+]>O>[NH2:4][CH:5]([CH3:18])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21419358HCID 21419358, compound

Product 1

HCID 19690917HCID 19690917, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 29 g. of residual oil described in Example 3 above (ethyl ester of rac. 4-(2-acetamidopropyl)phenoxyacetic acid was refluxed with 16.4 g. of sodium hydroxide (0.41 moles) in 150 ml. of water for 15 hrs., after which the solution was cooled, a trace of flocculent matter removed by filtration and the clear filtrate passed over a column of 750 ml. (0.75 eq) of Dowex® 2-X4 in the hydrogen form. After washing the column with water until the effluent pH was 4-5, the amino acid was eluted with 2 l. of 10% aqueous pyridine. Distillation of the pyridine effluent in a rotary evaporator left a residue of 18 g., m.p. 301°-303° dec.

Workup

  1. temperaturewas refluxed with 16.4 g
  2. temperature, after which the solution was cooled
  3. customa trace of flocculent matter removed by filtration
  4. washAfter washing the column with water until the effluent pH was 4-5
  5. washthe amino acid was eluted with 2 l
  6. distillationDistillation of the pyridine
  7. customeffluent in a rotary evaporator
  8. waitleft a residue of 18 g

Sources & evidence

ORD record
ord-b94910a2b6fe40539dcbdde5e1ed616d
Source dataset
uspto-grants-1977_08
Patent number
US04041076

Reaction notes

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